cross dressing your 1st time

[jackbirdjay]

How many guys love to cross dress? When was your 1st time? I was 14 my 1st time, moms things. Dad died when I was 13 so mom worked a lot. I was home alone a lot. Started going though her things. She had lots of girdles, stockings, garters, and sexy bras. Started wearing them and use to jerk-off wearing them. Then in my 20's had my own place started wearing all the time. I started wearing panties 24/7 and as soon as I would get home from work get dressed in bras, garters, stockings, and even heels. At 20 sucked my 1st cock and started seeing older married guys. It was a power thing getting dressed for them and giving them pleasure. I am now married to a nice women that dosen't know about my past. I do dress sometimes in secret. I know my wife wouldn't understand it because I tested the waters with her. She thinks its sick to cross dress. What do u think???????

[elian]

I think about the same age or a little younger I experimented with the same thing..and at that age I was passable. I think I was jealous of the way women could attract men, and what I thought of at that VERY young time in my life as an "easier" life. I have since learned that women absolutely do not have an "easier" life, and now with much more hair I find that it is just easier to live with the factory installed equipment. Having grown up with very poor male role models it has been an interesting ride learning to just accept myself for who I am.

Having said all of that, I do know there are guys who dress up simply because they like the feeling of being in female clothes - even met a group of guys who have no same sex feelings of attraction but still enjoy cross-dressing.

I guess as long as you aren't hurting anyone else why should you feel ashamed? I know at one point I had a girlfriend when I was going through that phase that not only tolerated but actively participated in my CD experiments - she was also just as young so maybe that is the difference.

I'm sure your spouse has very specific ideas about what their perception of a "man" is - doesn't mean it couldn't change but I don't know your circumstances. Someone else here who is in a married relationship could probably better speak to that experience.

[meflash]

I didn't start to CD untill just 2 yrs ago at 51. After my 25yr marriage ended & now being single I wanted to explore my bi feelings. I slowly meet a few guys & did enjoy the sex mostly nudr get togethers watch porn jo oral, no kising or cuddling like with a woman. I meet a guy who after our first meet called me & asked if I would be open to ware stockings & panties for him, he said That I had the body for them. I ageed to do it, went out & bought them. At our next meet I changed into them I felt very horny doing it & he really liked my look. He asked for more cloths so i got bra garters short skirt & frilly top. I was dressed up for our next meet & as soon as he came in I closed the door dropped to my knees & gave him a great bj, I felt so submissive & when iam not dressed iam not like that. Next came the wig makeup & at our last next I let him have anal sex with me,for omly the second time in my life. That was our last meet with him & now I dress up for a few friends on cam. CD for me is a sometime thing I don't want to change into a woman but from time to time i wish to meet up again with someone I can be his submissive girl for a hot sexual meet

[mikey3000]

For the first time, three days ago my wife asked my to put on her panties, and she put my umderwear on. Sexy!!!!! Hers are so soft and silky, felt so gentle. She liked mine too. We actually went to the mall like that. It was so cool sharing a little secret like that in piublic. I just prayed we didn't get hit by a bus or something and have to be rushed to the hospital. We'd have a haed time explaining the underwears.:bigrin:

[jackbirdjay]

I didn't start to CD untill just 2 yrs ago at 51. After my 25yr marriage ended & now being single I wanted to explore my bi feelings. I slowly meet a few guys & did enjoy the sex mostly nudr get togethers watch porn jo oral, no kising or cuddling like with a woman. I meet a guy who after our first meet called me & asked if I would be open to ware stockings & panties for him, he said That I had the body for them. I ageed to do it, went out & bought them. At our next meet I changed into them I felt very horny doing it & he really liked my look. He asked for more cloths so i got bra garters short skirt & frilly top. I was dressed up for our next meet & as soon as he came in I closed the door dropped to my knees & gave him a great bj, I felt so submissive & when iam not dressed iam not like that. Next came the wig makeup & at our last next I let him have anal sex with me,for omly the second time in my life. That was our last meet with him & now I dress up for a few friends on cam. CD for me is a sometime thing I don't want to change into a woman but from time to time i wish to meet up again with someone I can be his submissive girl for a hot sexual meet

yes know what u mean

[bistraightpat]

I started at 15 with my moms stuff. Wore a lot of sexy stuff but I really like just normal dresses. Sometimes for me that's better than lingerie. I may not always looks good in them but I feel great.

[roy m cox]

i started at 5 or 6 i loved wearing my sisters skirts and some of her bikinis they always felt good to me of cores i had a good resin why i started

http://www.youtube.com/watch?v=2IQmEwK6I20&feature=related :eek:

[bikiniman]

I tried on a pair of my sisters bathers when I was about 17. Now 40+ I enjoy putting on my wifes bikinis when she is not home. My wife knows that I tried on my sisters bathers but does not know that I like wearing hers.

Is it sick? No I do not think it is sick. Women can wear mens underwear eg "Boy shorts" where's the lingerie for men?

[19biman61]

My sister dressed me up as a girl when I was about three or four. I used to wear her clothes when she wasn't home. When I got older and she got married, I started wearing my mothers clothes. I wore my wife's stuff when we were married, now I have my own wardrobe and dress when I'm home. I love the feel and the look. I'm not passable so when I go out I only wear panties and thigh highs under my clothes.

[Caity]

When I was around 9 years old, I tried on my cousins bikini.

[newyorker]

I like to ware panties and stockings under my clothes when I go out. I could never pass for a woman and don't want to be one. I just like the feel of the silky underware.
I did it for the first time when I was 25 for about 2 years. Then didn't again until several years ago. I wish to find a guy who likes it also. I am submissive with a man. I like being the one being told what to do. Not like that with women or in public. Something about being on your knees and being told to do what the guy wants.

[Samantha Sabrina]

I posted much more to this on another thread so I will just touch a few high points here.

My "First" time dressing enfemme I was 18 and in the Marines, without going into great detail, (still classified), I went thru a course on how to change my appearance, and the very first thing they did was stick me in a dress, pantyhose, bra, wig, makeup, and heels, then stood me in front of a full length mirror, my jaw about hit the floor.

I basically got a 30 second snap shot of what I looked like as a female, and that has been stuck in my head ever since, (they changed to all kinds of different guy things, facial hair, clothes, all kinds of things), well I lived as a male until about 3 years ago, and I finally was able to grow facial hair and everything, (takes forever but it does grow, lol), anyway all these years I have been able to pretty much live all the different looks and styles men can look like, everything from classy businessman to total bum and even rough and tough biker, this was allowed in public, so no problem, but behind closed doors I always wanted to see that female I saw for 30 seconds again, and I sorta played at it off and on thru the years but never did go all out like they did, wig, makeup and all that.

I am on my 3rd marriage, and 3 years ago I decided that I really wanted to see that "girl" in the mirror again, and I was not getting any younger so it is now or never, sooooooo, I took the plunge.

I was trucking coast to coast and started dressing in the sleeper, then started driving dressed, and I found out I enjoyed it, and felt very much at home and comfortable with it.

I decided it was time to cut my female side loose completely and get her out of the closet, now understand I Love my wife dearly, but I had already lived 50 years of my life to suit everyone else, got my son raised, so I figured it was my turn, and decided I would tell my wife, she is 10 years older than I am, and I honestly did not expect her to leave me over this, I expected her to say whatever just don't let me see it kind of thing, but I was also prepared for her to leave me if it came to that.

Luckly for me not only didn't she leave me, but she has understood, helped, supported, and even embraced Samantha, (it did take awhile for most of that though).

When I told her I had already thought long and hard about how I would control the conversation and make my case to her, and it went rather well actually, but the biggest point I was able to use that made her cock her head to the side and got the lil light to come on, (as in oh I got it now!), I simply pointed out to her that she as with all women are allowed to wear anything they want, INCLUDING male clothing and that actually the more "Male" they dress the more people say OMG isn't she just the cutest thing.

I went onto point out to her that she has been "Crossdressing" most if not all her life, and certainly ever since we got married and not once have I ever thought less of her for it, that is what got her to thinking, and realized I was right.

She had many male clothing items, jeans, tee shirts, underwear, coats, flannel shirts, shoes and boots, and it was ok for her to wear those, so why would it not be ok for me to wear female clothing?

It has worked out great for us, and she has actually realized there are a shit load of benifits to me living like this, lol...including being much easier to live with, and Samantha LOVES shopping where my guy side flat out HATES it.

I know I tend to get pretty long winded with my postings but sometimes things just can't be said with a few words, giggles.

For those of you that are not able to be yourself openly and freely I honestly feel for you, been there done that, and it SUCKS.

I wish you all good luck in getting that closet door open SOON.

Hugggggggggggs

Samantha